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IMIKNYLMKTIIYLTRIAZOLE CARBOXVLIC ACID    233
The phenylhydrazine and bydrocbloric acid are mixed
together, stirred mechanically and cooled witb a few lumps of
ice whilst the nitrite solution is added, until the test with starch-
iodide paper shows that an excess is present. The hydro-
chloride dissolves, and diazobenzolimidc separates out as an
oil.
/N
C(!n,Nn.NH.,+ nNOo-Cr!I.N<   || +2l-I,O
\N'
Part of the  water is removed by a syphon and the oil is
extracted with ether ; after removing the ether, the diazobenzol-
imide is purified by distillation in steam.    l\ is again extracted
and separated witb ether as before.    Yield, about 25 grams.
4 grms. sodium.
68 c.o. absolute alcohol.
22 grins, acctoacetic ester.
20     Ą     diazobcnzolimide.
The sodium is dissolved in the alcohol, and to the cold solu-
tion a mixture of the acctoacetic ester and diazobenzolimicle
is added, and then warmed to boiling with reflux condenser.
As soon as this occurs, the tla.sk is removed and cooled, if the
action becomes too violent. After the reaction is over, the
mixture is heated, for an bour on the water-bath with reflux con-
denser, when the contents of the flask become almost solid. The
mass is dissolved in the smallest quantity of hot water, and the
liquid, if neutral, made strongly alkaline and boiled again for an
hour. About 350 r.c. bot water arc added, and sufficient hydro-
chloric acid to precipitate the triaxolc carboxylic acid. It is
filtered and washed with a little water, and is then nearly pure ;
m. p. 155". Yield, about 27 grams.
M.C:,,!!,,                                 N.QH,
//    '             X\
N/    ~r         ,    rHON       "N     C.CH:i + 2C,HflOH.
H/CO.CH,,   "h   ca"f,ONa..... y       ^
N       !         "                          NóC.COONa
CIUCOOCUL,
See Appendix, p. 320.